Trifluoroacetic acid → 2-cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid carbamoylmethyl-amide

HRID 446940Notes

Reaction equation

HRID 446940 reaction equation
[C:1]([CH2:3][NH:4][C:5]([C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([CH:16]3[CH2:18][CH2:17]3)[N:14]=2)[N:9](COCC[Si](C)(C)C)[CH:8]=1)=[O:6])#[N:2].FC(F)(F)C(O)=[O:30]>C(Cl)Cl>[C:1]([CH2:3][NH:4][C:5]([C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([CH:16]3[CH2:18][CH2:17]3)[N:14]=2)[NH:9][CH:8]=1)=[O:6])(=[O:30])[NH2:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 866576262-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid cyanomethyl-amide

Product 1

HCID 533897902-cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid carbamoylmethyl-amideYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid cyanomethyl-amide (0.19 g, 0.50 mmol) in CH2Cl2 (6 mL) was added trifluoroacetic acid (1.0 mL). The reaction mixture was stirred at room temperature overnight then concentrated. The residue was dissolved in MeOH (10 mL) and H2O (2 mL) and Et3N (2 mL) were added. The reaction mixture was stirred at room temperature overnight then concentrated. The residue was triturated with EtOH to afford 0.093 g (77%) of 2-cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid carbamoylmethyl-amide as a light yellow solid. MS: (M+H)+=260; mp=215.0-220.0.

Workup

  1. concentrationthen concentrated
  2. dissolutionThe residue was dissolved in MeOH (10 mL)
  3. additionH2O (2 mL) and Et3N (2 mL) were added
  4. stirringThe reaction mixture was stirred at room temperature overnight
  5. concentrationthen concentrated
  6. customThe residue was triturated with EtOH

Sources & evidence

ORD record
ord-cfe51aadd27a40c0bc2b7baee2d6f0ec
Source dataset
uspto-grants-2013_07
Patent number
US08481541B2

Reaction notes

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